peficitinib   Click here for help

GtoPdb Ligand ID: 8315

Synonyms: ASP015K | JNJ-54781532
Approved drug Immunopharmacology Ligand
peficitinib is an approved drug (Japan (2019))
Compound class: Synthetic organic
Comment: Peficitinib is an oral Janus kinase inhibitor [5] that was developed for potential anti-inflammatory action in autoimmune diseases including rheumatoid arthritis [6-7], psoriasis and ulcerative colitis [3].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 104.03
Molecular weight 326.17
XLogP 1.83
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)c1cnc2c(c1NC1C3CC4CC1CC(C3)(C4)O)cc[nH]2
Isomeric SMILES NC(=O)c1cnc2c(c1NC1[C@@H]3CC4C[C@H]1CC(C3)(C4)O)cc[nH]2
InChI InChI=1S/C18H22N4O2/c19-16(23)13-8-21-17-12(1-2-20-17)15(13)22-14-10-3-9-4-11(14)7-18(24,5-9)6-10/h1-2,8-11,14,24H,3-7H2,(H2,19,23)(H2,20,21,22)/t9?,10-,11+,14?,18?
InChI Key DREIJXJRTLTGJC-JQCLMNFQSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Peficitinib was approved as a treatment for rheumatoid arthritis in 2019 [4], but is not yet (March 2021) approved by the FDA or EMA.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The Janus kinase (JAK) enzymes play a key role in cytokine signalling, which is involved in the pathological symptoms of immune-mediated disorders such as rheumatoid arthritis (RA). Peficitinib has been reported to inhinit all four JAKs at low nanomolar concentrations, although this data is not yet published in a peer reviewed article (see ASP015K: A Novel JAK Inhibitor Demonstrated Potent Efficacy in Adjuvant-Induced Arthritis Model in Rats, an abstract from the proceedings of the American College of Rheumatology/Association of Rheumatology Health Professionals, Annual Scientific Meeting, Washington DC, November 9-14, 2012).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02308163 A Study to Evaluate Safety and Efficacy of ASP015K in Patients With Rheumatoid Arthritis (RA) Who Had an Inadequate Response to DMARDs Phase 3 Interventional Astellas Pharma Inc 8
NCT01711814 A Study to Evaluate the Long-term Safety and Efficacy of ASP015K in Subjects Previously Enrolled in a Phase 2 ASP015K Rheumatoid Arthritis Study Phase 2 Interventional Astellas Pharma Inc 1